


Where's the line?

by lol_lee_lol



Category: Awkward. (TV)
Genre: F/M, Menstruation, PWP, Pictures
Language: English
Status: In-Progress
Published: 2018-01-25
Updated: 2018-04-12
Packaged: 2019-03-09 04:47:24
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 3,538
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13474002
Author URL: https://archiveofourown.org/users/lol_lee_lol/pseuds/lol_lee_lol
Summary: Jenna was never really able to say no to Matty. Little by little, he comes up with new stuff. New ideas for them to try. Will she be able to stop him at some point?





	1. Just a picture

I was sitting in my bed when my phone rang. It was Matty. Of course it had to be him. Just when I was thinking about leaving him. Well ... not that we were really together.

\- Hi sexy  
\- Good morning.  
\- I miss your pretty face  
\- Yeah, im sure thats what you miss the most 

It took him a moment to answer me back. Just long enough for me to start to me stressed out. I was sure I had pushed too hard and that he’d be mad–the idea of leaving him sure left fast–but it was not the case. When I received the next text, instead of him giving me a lecture, it was a picture. Him, in his bed, without a shirt, still with his morning hair. Words quickly followed the picture: 

\- Youre right my bed does feel empty without you and your sexy ass.

It was the first picture Matty decided to send me and what a picture it was. I looked to my left at my closed bedroom door. Than at myself. Back at the door. One quick picture, what harm could it do? Not thinking much more about it, I threw away my shirt, readjusted my breast in my bra and turned on the selfie mode on my phone. With the amount of time he had seen me naked, it wouldn’t be that big of a deal. At least, that’s what I thought.

Not so long after hitting send, he thanked me for the picture and told me how pretty I was… Matty McKibben telling me that I was pretty… Me! Some things still had their effects. This is exactly when our new game started. McKibben: picture man. And not just any picture. Pictures of me. It continued telling me how it was not fair that he was topless and I still had my bra on. I tried to argue, but he sent me a picture of his hard-on through his pants and just like that, I was a goner. My boobs were out of the last fabric covering them and the picture was on its way. They were not big at all, but I liked them. The areola was a reddish-brown color and they seem to be just the perfect size to fit with the rest of my mount.

\- You have no idea how much this is going to help this morning.

Well, that sure was direct. I still decided to send him a smiley face though as I was still happy to know it excited him.

It stayed that way for a few days. By "that way" I mean that I only sent him a few more pictures of my breasts. I even let him take one while we were at the camp. Of course though it could not stay like this for long. I knew it was only a question of time I was not kidding myself. And that day came at the most unexpected moment. There I was, sitting in my bed, when he texted me that he could not wait for tomorrow.

\- Aunt Flo is in town :(  
\- Thats nice. How is she?  
\- No Matty. Im in the red zone.  
\- How much in the red? Were getting paid this Thursday

I was not sure how much clearer than that I could be without spilling it out for him. So this is exactly what I did.

\- Matty … sweety … im on my period. Menstruated. Blood coming out of my vagina.  
\- Oh! That’s ok :)

I sure hope it was. It is not like I had any saying in the matter. 

\- Can I get a picture? 

I expected it. I had taken it already. Zoomed in on the two girls. 

\- I mean lower  
\- Lower? I asked back, unsure what he meant.  
\- Of all of you  
\- Now? 

Usually, I would have said no without even thinking about it, but since I had just told him about my “situation” and he was still asking, it took me off guard.

\- Yes, if its not too weird :S

It was; not going to lie. Before I could answer back though, he came rushing back:

\- You can keep your panties on if you don’t feel comfortable, but I would prefer without.

What the fuck? OK, that was starting to be a bit too weird for me. Although as I was saying that to myself, my hands were stripping my body and, before I knew it, I was only wearing a bra and my socks. This guy was weird. Yet I probably was not better.

I looked at the picture I had just taken for a moment. It was starting roughly in the middle of my breasts going all the way down to my thighs. With my left hand, the one not holding the phone, I was very delicately pulling on the string that was coming out of me. Just hard enough so that it was straight. Hesitant, I still hit send.

\- My god youre amazing.

It barely took him any time to answer. Quickly adding a "thank you" after. I let him a moment to look at the picture before I hit him:

\- Are you turned on by it?  
\- You always turn me on.  
\- I mean menstruation.  
\- Oh...

That's it? "Oh"? That certainly was not the answer I was expecting. I don’t know what I was expecting, but at least an answer. Some actual words.

\- I never minded it, but everyone seem to be close to everything anytime this time of the month come around.

I was too. I always had been. Never even considered trying to masturbate while in it. It sounded gross. I was not going to tell him though.

\- Dont worry though. We will still find a way to make you come ;)

I giggled at my own comment as I was dressing back up. Once back under the cover, I looked at my phone.

\- Trust me, you already did.

With that, he attached a picture of his hand covered in sperm. I smiled to myself. Matty McKibben had come while watching me. It was not the first time, but it was still special. There was no reason why he would like me like that. He was fucking Matty McKibben after all. Happy, I fell asleep.

\---

The following day went by way too slowly for my liking. All day, I had to watch Matty with his ... too perfect face without being able to touch him. Of course, he could not really touch me today, but I did not care. Simply kissing him would be amazing. As soon as we were able though, we had disappeared. I had my head tilted up to kiss him. His tongue and mine were dancing as my hand was already under his shirt, touching his muscular chest. Why did periods have to exist? Nevertheless, my fingers were done reanalyzing his muscles and were working on bringing to life his little friend. My little friend. Not so little. At least, I think. It’s not like I had a lot to compare it to.

He lowered his pants. I took a hold of his cock, slowly masturbating him. A few seconds in this position before I removed my mouth from his, ready to get on my knees. To my surprise though, he spoke.

\- Can I see the girls? He asked. I was used to him calling my breast this way, but he never really asked for me to get them out. Ever. Although, I happily complied and I quickly was out of my shirt and bra. I was starting to think that he really liked my body, strangely.

\- Be quick, I ordered him as I dropped down.

We did not have all the time I would like right now. Thankfully though, I knew how his body worked. We had done this before. Over and over again. With his penis in my mouth and his balls in my hand, I was doing quick movement. I took it out and replace my lips with my right hand to speak to him.

\- Come on. Come for me. Let me swallow it all. Let me be your dirty little girl.

I was not the best at dirty talk, but I was doing my best. Back in my mouth he went. Looking up while bobbing it, he had his own head back; looking to the sky. Suddenly, without warning me, he took it out of my mouth. I was not lying before, he would usually make me swallow it. At least, at first he was making me. I quickly grew accustom to it and stopped minding the taste. Besides, with how much he seemed to like it, it helped me "appreciate" doing it.

\- What’s wrong? I asked, sharing a look with him.  
\- Let’s do it.  
\- Matty. I’m still on my period.  
\- Let’s still try it.

Not answering back, I took back his dick in my hand and started the really fast movement again, sometime licking the tip of it.

\- You want to fuck me? Is that what you want? Fucking my bloody pussy? Making me come all over your cock.

That did it. I felt him being there. I quickly put the gland between my lips, catching the four streams of sperm. The good thing about swallowing is the lack of a mess afterwards. As I got back on my feet, he handed me a glass of water. He usually did that. I did not know if it was to make sure I had the mouth clean before kissing or to be kind, but I was supposing the latter. No matter what though, he was back glued to my lips as he picked me up so that I could sit on the table. His hand made its way under my pants.

\- Matty, I tried stopping him, getting muted by his mouth. Matty. I'm still...

I stopped myself as his finger made its way pass my second pair of lips. Too late. And too bad. There was no stopping now. Getting fingered never felt this good. Like all my nervous system was on high alert. He was still kissing me but I was not giving it back anymore. His finger was going in and out of me rather slowly. He drew back a little to look me into the eyes. A smirk on his face. I could not help but smile at him. He smiled back, getting it as my approbation. Getting out of me, he found once more my clitoris. As always, knowing what to do with it. With his thumb he was doing small and quick circles on it. Just on the edge of coming, I had the reflex of grabbing my shirt to put it over my mouth. Yelling inside of it. I knew I could not have kept it down. This was by far the best orgasm I had. I wanted more. And more. But he was done. His hand was out and he was rinsing it. I quickly put my bra and my shirt back on. I knew the drill by now. After stealing him one last kiss, we were out the door as if nothing happened.


	2. A new kind of picture

**Summary for the Chapter:**

> Matty is starting to reach for the moon as he tries to convince Jenna to send him a picture of something else.

Jenna that tried to kill herself. I knew it could not be true, yet I could not get it out of my head. I was more or less texting her just as Jake was changing right next to me. It was not the first time seeing him in his briefs. I never cared before nor did I now. Although, an idea formed in my head.

"Hey! Smile for the camera," I told him. He did not question it, looking at me, still half-naked, doing finger guns with his hand and smiling.

"Why?" he finally asked after the picture was taken.

"So that we can find you a girlfriend."

After a few reprimands from him, I told him the picture was gone before ordering him to hurry up. As he was dressing back up, I texted the picture to Jenna with the caption "hope you like." I did not wait to see her answer. Putting the phone back into my pocket, we both left.

When I finally picked it back up, she only had sent me one SMS: "I think you have the wrong person :P". Pretty much the best answer she could have said. The answer was obvious: "No. Youre such an amazing girl. I felt we were at the point I could share those kinds of things with you. Dont worry though. You dont need to send anything back if youre not ready. As long as I can keep getting more of you."

Silence. I know it was far-fetched to assume she would fall for such a trick, but it was worth a try. After a few minutes, she was back: "I did not know people usually do that. But I love that you feel comfortable enough to send me this. Of course I’m ready. I'll figure out a way to get one. Whom do you want to see the most? T or Ming?"

Really? How could she fall for that? Anyhow, little Maddie was already getting hard. Tamara obviously, but I was not that stupid.

\- You obviously!  
\- Awww. Mattie. You’re making me blush.  
\- Its only the truth.

It took a moment before she texted me back. She sent me a picture zoomed in mostly on her boobs, still letting me see the beginning of her cast. She had cute small breasts, but I liked them. Seeing how I was not answering right away - busy watching her body - she texted me: "hope they can keep you waiting."

\- not really. Now I just want to be next to you to put them in my mouth.  
\- Silly.

We talked a bit about nothing and everything before she told me that Tamara was there. It barely took me a second to think about getting a picture of her, but I did not say anything. I simply told her to have fun, hoping the impossible would happen.

It did not. Of course not. Roughly two hours after her friend arrived, I noticed how silly I was being and, at 10 ish, when she texted me, I was not hoping for it anymore. I knew it had been a stupid idea. After a few back and forth, she texted me the unthinkable:

\- Sorry that I couldn’t take your picture. It’s hard to fit in the conversation "sorry. Can you flash me your boobs so that I can send them to Matty?"  
\- It was not supposed to put pressure on you. Dont worry about it. As long as I keep getting you, i dont need the others.

She was really thinking about it. Thinking about showing me her friend. That was kind of a dream come true to have someone like that.

\- You’ll get it at some point, don’t worry. It’s not because I don’t want to move forward that I’m not giving it to you. Next time we are alone we could even try this :$

Following her blushing emoji was a picture of her ass. A bit out of frame, but it was the meaning behind it that was important. I had tried to get her to do anal before. I always wanted to do it but no one ever let me put a single finger near that hole, let alone my cock.

\- Are you for real?  
\- I know it’s not quite the same but I was hoping it would help you wait...  
\- I would love that

She still had a bit of self-esteem issues. I did not mind. It did not seem too bad. Pulling my cock out of my pants, I started wanking to the picture of her butt.

\- It's been a long time since I haven’t had a picture of you.

It was rare that she asked for one. As an immediate answer though, I turned on the camera and captured my already hard cock.

\- Am I the one that gave you that effect?  
\- you bet your sweet ass you are.

I kept on going just as I unexpectedly got a pictured of her closely shaved pussy, with two wet fingers getting out of it. Carefully saving it in a hidden folder on my phone - just in case someone was to look at my pictures - I kept going, looking at her body. It was not long before I came on my stomach. Taking my phone, I tried to take a picture of the mess with my cock lying near it before I went soft again. I was barely in time.

\- Look at what you made me do.

With that, I joined the picture that I just took. She did not answer right away. After a while, a zoomed-in picture of her lips with the two same finger than earlier in it. With that, she said that at least she could clean up her own mess with her mouth.

\- I wish you would have been there to clean mine too  
\- Usually a lot less messy when we're together though.  
\- Thats because your the best

I closed my phone, assuming the conversation was over. It took half an hour for it to vibrate again. I did not even expect it to be her.

\- It's "you're.”

I laugh as I received a second SMS.

\- You'll get it soon. But for now it can help you wait a little I hope.

I was not sure why she was coming back on the subject of the picture now. I only understood what she was referring to because of the few pictures that were joined to it. Her, Tamara and Ming, in their bathing suit, outside, taking pictures of each other. I texted her back with a quick thank you but that I was not in a rush. I looked at the screen. This is when I should have shut it. Just considered it as enough. I had been far enough, and it would even award me anal. What more could I ask for? I did not follow my own advice and decide to risk everything.

\- Would you like a naked picture?

I asked, careful to word it pretty badly.

\- Yes! Of course! :D  
\- Good. I dont know if I can ask him tomorrow, but if you let me a few days, ill send you his cock :)

I had to wait a few seconds. After that she sent me a bunch of short text messages really quickly.

\- Wait what?  
\- What do you mean?  
\- No.  
\- You.  
\- I thought you meant you

And then: A really short pause. I was about to answer when she texted again. The most surprising answer.

\- Wait. You would really do that?

For once, I took a moment to weigh my words. I was not exactly lying. Sure, it was all to see her friend, but I was down to send her one if it meant seeing how Tamara looked like in her birthday suit. I could not tell her that though. How could a girl react positively to that kind of sentence?

\- Of course. I would totally understand if you were curious and wanted to see it. We all are. 

I waited for a bit and added an "I trust you.” It took her a moment to answer me.

\- I trust you too. You wouldn’t get those pictures otherwise.  
\- Of course. I know you do. Its the mutual trust that helps the pictures too.

After that we diverged a little before the conversation ended.

The following day, she texted me the most surprising thing.

\- I'm still working on it, I know it’s not the same, but I bet it can make you wait a little more.

I did not get a chance to look and the pictures she had joined though. I wrongly assume it was her. I went through my day without thinking twice about it. When I finally got home, ready to masturbate in front of some porn, I thought I could watch her picture first to get me into the mood. I liked her, but always watching the same girl could get old sometime.

This is when my jaw dropped to the floor. It was not her. She had taken her phone into the locker room and snapped a few pictures of the girls changing. A few bras, a few G-strings and a really solid hard-on for me. I wanted to thank her, but not yet. My left hand had already successfully unbuckled my pants and I was lying on my bed when I switched the phone to my other hand. Neither of her friends was in the picture, but Sadie was there. At first, when I went over the picture, it felt wrong, but the feeling did not last and I soon was scotched to the picture, furiously making arms movement. It did not take long to ejaculate while watching her breast hidden by a gray bra.

As I was reaching over and grabbing a facial tissue, I thought of Jenna. She was something special. I always liked her, but now it felt like it was getting more than that. I would not tell her though. Not now. Not until I would be absolutely sure. I would not want it to be simply because she sent me the pictures and get her hopes up for nothing.

**Notes for the Chapter:**

> Don’t worry. It’s not only about Matty getting pictures. There will be more action in the next chapter.

**Author's Note:**

> First time writing on my phone. I tried to correct it afterwards on my computer, finding a few synonyms, but it might not be on point yet. I'll get there soon enough.


End file.
